Synthesis and characterization of the hexenuronic acid model methyl 4-deoxy-β-L-threo-hex-4-enopyranosiduronic acid

被引：17

作者：

Adorjan, Immanuel ^{[1
]}

Jaaskalainen, Anna-Stiina ^{[1
]}

Vuorinen, Tapani ^{[1
]}

机构：

[1] Helsinki Univ Technol, Dept Forest Prod Technol, FIN-02015 Helsinki, Finland

来源：

CARBOHYDRATE RESEARCH | 2006年 / 341卷 / 14期

基金：

芬兰科学院;

关键词：

TEMPO oxidation; beta-elimination; characterization by FTIR; Raman; UVRR; NMR;

D O I：

10.1016/j.carres.2006.06.012

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 [生物化学与分子生物学]; 081704 [应用化学];

摘要：

A facile synthetic scheme for the preparation of methyl 4-deoxy-beta-L-threo-hex-4-enopyranosiduronic acid utilizing the commercially available methyl a-D-galactopyranoside as starting material has been developed. The synthesis sequence comprises six high yielding reaction steps: TEMPO oxidation, acetylation, methanolysis of the lactone, acetylation, P-elimination, and final removal of the protecting groups. Only one column chromatographic purification is needed throughout the whole sequence. The overall yield is 60%. The final product has been characterized by NMR, Raman, UVRR, FTIR, and HRMS. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：2439 / 2443

页数：5

共 22 条

[1]

BASE-CATALYZED DEGRADATIONS OF CARBOHYDRATES .9. BETA-ELIMINATIONS OF 4-O-SUBSTITUTED HEXOPYRANOSIDURONATES [J].

ASPINALL, GO ;

KRISHNAMURTHY, TN ;

MITURA, W ;

FUNABASHI, M .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1975, 53 (14) :2182-2188

[2]

Regio and stereoselective conversion of Delta(4)-uronic acids to L-ido- and D-glucopyranosiduronic acids [J].

Bazin, HG ;

Kerns, RJ ;

Linhardt, RJ .

TETRAHEDRON LETTERS, 1997, 38 (06) :923-926

[3]

Conformational study of synthetic Δ4-uronate monosaccharides and glycosaminoglycan-derived disaccharides [J].

Bazin, HG ;

Capila, I ;

Linhardt, RJ .

CARBOHYDRATE RESEARCH, 1998, 309 (02) :135-144

[4]

BETA-ELIMINATION IN URONIC ACIDS - EVIDENCE FOR AN ELCB MECHANISM [J].

BEMILLER, JN ;

KUMARI, GV .

CARBOHYDRATE RESEARCH, 1972, 25 (02) :419-428

[5]

BUCHERT J, 1995, TAPPI J, V78, P125

[6]

CHERNYAK AY, 1988, SER KHIM, V7, P1660

[7]

deNooy AEJ, 1996, SYNTHESIS-STUTTGART, P1153

[8]

HIGHLY SELECTIVE NITROXYL RADICAL-MEDIATED OXIDATION OF PRIMARY ALCOHOL GROUPS IN WATER-SOLUBLE GLUCANS [J].

DENOOY, AEJ ;

BESEMER, AC ;

VANBEKKUM, H .

CARBOHYDRATE RESEARCH, 1995, 269 (01) :89-98

[9]

Variables affecting the thermal yellowing of TCF-bleached birch kraft pulps [J].

Granström, A ;

Eriksson, T ;

Gellerstedt, G ;

Rööst, C ;

Larsson, P .

NORDIC PULP & PAPER RESEARCH JOURNAL, 2001, 16 (01) :18-23

[10]

Jiang ZH, 2000, TAPPI J, V83, P167

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